I'd like to know what gift I'm getting before I decide. You know, if it's a really good one, then yeah. But if it's one of those cheesy ones like you get at the office, then hell no!
PS: I wear a size 911 in Porsches ;- )

Thank you for taking the time to respond! I am very excited to about this news - it honestly made my day. I'll be eagerly looking forward to it, and I would be happy to help if it's ever needed in any way at all. Take care!!

I try to veer away from "let's do it like so-&-so" examples; however, if we must, then I am inspired by Reddit Gifts. I would be over joyed by a community gift giving event(s) on MassDrop. I like your idea of MD being the mediator between us for the sake of privacy... I also think that whether all communities were pooled together for this, or it was done individually on a per-community basis, we could still make it work. If all communities are grouped together for, say, a Secret Santa, then all that we have to do is answer a questionnaire that will give some insight on what we are into and we will be grouped with somebody based off of that. It doesn't matter if Helen likes keycaps or not, all that she needs to know is that I like keycaps & boards. Then, she can go explore the Mech Keys community (or other places online) and decide from there what she wants to get me based off of any various factor from how much she wants to spend, to me noting in my questionnaire that I love ramen; so she buys me a ramen bowl artisan keycap. This also introduces Helen to new things that she never realized how interested in it she would actually become, such as mechanical keyboards. now she spends as much time in that community as she does knitting (:
If it is done with communities segregated, that makes it much easier. Same concepts though. The opportunities are sort of endless on this one. I would leave it to the MassDrop Gods to make the finer points of decision making.

Unfortunately, not everybody really checks the Talk section... There isn't much of a way to put this out there and see if anybody else is interested. So thank you for sharing any input at all in the first place. (: